Cyclohexene oxide → 2-(But-3-en-1-yloxy)cyclohexanol

Temperature

0 °C

To a mixture of cyclohexene oxide (3-1) (10.0 g, 102 mmol) in 3-buten-1-ol (17.4 mL, 204 mmol) cooled to 0° C. was added FeCl3 (1.65 g, 10.2 mol) The mixture was removed from the ice bath and stirred at rt for 1 hr. The reaction was quenched with water and extracted ether. The combined organics were washed with brine, dried, filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (400 MHz, CDCl3) δ 5.77-5.88 (m, 1H), 5.00-5.15 (m, 2H), 3.69-3.76 (m, 1H), 3.39-3.44 (m, 2H), 2.98-3.05 (m, 1H), 2.74 (s, 1H), 2.30-2.39 (m, 2H), 1.94-2.11 (m, 3H), 1.61-1.79 (m, 3H), 1.06-1.37 (m, 2H).

1. customwas removed from the ice bath
2. customThe reaction was quenched with water
3. extractionextracted ether
4. washThe combined organics were washed with brine
5. customdried
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by column chromatography

ORD record

ord-d972889f7d7a40909401873c2d5988f0

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829196B2